150114-71-9

Basic information

• Product Name: AMINOPYRALID
• Synonyms: AMINOPYRALID;2-Pyridinecarboxylic acid, 4-amino-3,6-dichloro-;2-Pyridinecarboxylicacid,4-amino-3,6-dichloro-(9CI);4-amino-3,6-dichloropicolinic acid;4-Amino-3,6-dichloropyridine-2-carboxylic acid;Aminopyralid Solution, 1000ppm
• CAS NO: 150114-71-9
• Molecular Formula: C₆H₄Cl₂N₂O₂
• Molecular Weight: 207.01
• Product Categories: AMINOACID;Agro-Products;Amines;Heterocycles
• Mol File: 150114-71-9.mol
• Article Data: 4

Chemical Properties

• Boiling Point: 432°Cat760mmHg
• Flash Point: 215.1°C
• Appearance: /
• Density: 1.705
• Vapor Pressure: 3.12E-08mmHg at 25°C
• Refractive Index: 1.669
• Storage Temp.: 0-6°C
• Solubility: DMSO (Slightly), Methanol (Slightly)
• PKA: 2.22±0.25(Predicted)
• Water Solubility: 2.48g/L at 18℃
• BRN: 12065018
• CAS DataBase Reference: AMINOPYRALID(CAS DataBase Reference)
• NIST Chemistry Reference: AMINOPYRALID(150114-71-9)
• EPA Substance Registry System: AMINOPYRALID(150114-71-9)

Safety Data

• Hazard Codes: Xi
• Statements: 36
• Safety Statements: 26
• WGK Germany: 3
• Hazardous Substances Data: 150114-71-9(Hazardous Substances Data)

Usage

Description

Aminopyralid, an organochlorine pesticide, is characterized by its 3,6-dichlorinated 4-aminopicolinic acid structure. It is a chemical compound that has been developed for specific applications in the agricultural industry, particularly as a herbicide.

Uses

Used in Agricultural Industry:
Aminopyralid is used as a herbicide for industrial vegetation and pastures. It is effective in controlling woody plants, clovers, and thistles. As a systemic, post-emergence herbicide, it is absorbed by the roots and leaves of the targeted plants, leading to their control and management. However,

Flammability and Explosibility

Nonflammable

Trade name

BANISH?; FOREFRONT?; HALCYON?; MILESTONE? VM; PHARAOH?; PRO-BANISH?; RUNWAY?; SYNERO?; UPFRONT?

InChI:InChI=1/C6H4Cl2N2O2/c7-3-1-2(9)4(8)5(10-3)6(11)12/h1H,(H2,9,10)(H,11,12)

Synthetic route

4-amino-3,5,6-trichloropicolinate sodium → aminopyralid (150114-71-9)

Conditions	Yield
With sodium hydroxide In water at 35 - 40℃; for 3.33333h; pH=12.5; Temperature; pH-value; Electrochemical reaction;	96.4%

4-amino-3,5,6-trichloro-2-pyridinecarboxylic acid monopotassium salt (2545-60-0) → aminopyralid (150114-71-9)

Conditions	Yield
With potassium hydroxide In water at 45 - 50℃; for 6.66667h; pH=12.7; pH-value; Electrochemical reaction;	94.1%

picloram (1918-02-1) → aminopyralid (150114-71-9)

Conditions	Yield
With 5%-palladium/activated carbon; hydrogen; sodium hydroxide In water at 50℃; under 1500.15 - 2250.23 Torr; for 20h; Reagent/catalyst; Pressure; Temperature;	91.4%
With sodium hydroxide In water at 35 - 38℃; for 36h; Product distribution / selectivity; Electrochemical reaction;
With sodium hydroxide; sodium chloride In water at 35 - 38℃; for 24 - 46h; Product distribution / selectivity; Electrochemical reaction;

aminopyralid (150114-71-9) → 3,4,6-trichloropyridine-2-carboxylic acid

Conditions	Yield
With hydrogenchloride; copper(l) chloride; sodium nitrite In water for 2h; Time; Cooling with ice; Industrial scale;	91.7%
With hydrogenchloride; sodium nitrite In water at 0 - 100℃; for 3h; Temperature;	81%

methanol (67-56-1) + aminopyralid (150114-71-9) → methyl 4-amino-3,6-dichloropyridine-2-carboxylate (350601-39-7)

Conditions	Yield
With sulfuric acid for 24h; Reflux; Inert atmosphere;	81%
With thionyl chloride at 65℃; for 12h; Cooling with ice;

aminopyralid (150114-71-9) + Selectfluor (140681-55-6) → 4-amino-3,6-dichloro-5-fluoropyridine-2-carboxylic acid

Conditions	Yield
In sodium hydroxide; diethyl ether; acetonitrile	11%

aminopyralid (150114-71-9) → 4-amino-3,6-dichloro-5-fluoropyridine-2-carboxylic acid

Conditions	Yield
With Selectfluor In water at 20 - 65℃; for 24h;

aminopyralid (150114-71-9) + Selectfluor (140681-55-6) → methyl 4-amino-3,6-dichloro-5-fluoropicolinate (496850-09-0)

Conditions	Yield
In methanol; (2S)-N-methyl-1-phenylpropan-2-amine hydrate; water; ethyl acetate

aminopyralid (150114-71-9) + 2-Ethylhexyl alcohol (104-76-7) → 2-ethylhexyl 4-amino-3,6-dichloropyridine-2-carboxylate (350601-37-5)

Conditions	Yield
With sulfuric acid

aminopyralid (150114-71-9) + trimethylsilyl diazomethane + conc. HNO3/H2SO4 → methyl 4-Amino-3,6-dichloro-5-nitropyridine-2-carboxylate

Conditions	Yield
With sulfuric acid In methanol; diethyl ether; ethyl acetate

aminopyralid (150114-71-9) → 4-amino-3,6-dichloro-5-fluoropyridine-2-carboxylic acid + picloram (1918-02-1)

Conditions	Yield
With Selectfluor In water at 25 - 65℃;	A 40 %Chromat. B 4.5 %Chromat.

aminopyralid (150114-71-9) → methyl 4-acetamido-3-chloro-6-phenylpicolinate

Conditions	Yield
Multi-step reaction with 3 steps 1: sulfuric acid / 24 h / Reflux; Inert atmosphere 2: 16 h / Reflux 3: potassium fluoride; bis-triphenylphosphine-palladium(II) chloride / water; acetonitrile / 0.33 h / 110 °C / Microwave irradiation; Sealed tube View Scheme

aminopyralid (150114-71-9) → methyl 4-acetamido-3-chloro-6-(4-chlorophenyl)picolinate (496850-56-7)

Conditions	Yield
Multi-step reaction with 3 steps 1: sulfuric acid / 24 h / Reflux; Inert atmosphere 2: 16 h / Reflux 3: potassium fluoride; bis-triphenylphosphine-palladium(II) chloride / water; acetonitrile / 0.33 h / 110 °C / Microwave irradiation; Sealed tube View Scheme

aminopyralid (150114-71-9) → methyl 4-acetamido-3-chloro-6-(4-chloro-2-fluorophenyl)picolinate (496850-54-5)

Conditions	Yield
Multi-step reaction with 3 steps 1: sulfuric acid / 24 h / Reflux; Inert atmosphere 2: 16 h / Reflux 3: potassium fluoride; bis-triphenylphosphine-palladium(II) chloride / water; acetonitrile / 0.33 h / 110 °C / Microwave irradiation; Sealed tube View Scheme

aminopyralid (150114-71-9) → halauxifen methyl ester

Conditions	Yield
Multi-step reaction with 4 steps 1: sulfuric acid / 24 h / Reflux; Inert atmosphere 2: 16 h / Reflux 3: potassium fluoride; bis-triphenylphosphine-palladium(II) chloride / water; acetonitrile / 0.33 h / 110 °C / Microwave irradiation; Sealed tube 4: acetyl chloride / methanol / 6 h View Scheme
Multi-step reaction with 2 steps 1: thionyl chloride / 12 h / 65 °C / Cooling with ice 2: potassium fluoride; bis-triphenylphosphine-palladium(II) chloride / water; acetonitrile / 4 h / Reflux View Scheme

aminopyralid (150114-71-9) → methyl 4-amino-3-chloro-6-phenylpicolinate (496850-14-7)

Conditions	Yield
Multi-step reaction with 4 steps 1: sulfuric acid / 24 h / Reflux; Inert atmosphere 2: 16 h / Reflux 3: potassium fluoride; bis-triphenylphosphine-palladium(II) chloride / water; acetonitrile / 0.33 h / 110 °C / Microwave irradiation; Sealed tube 4: acetyl chloride / methanol / 6 h View Scheme

aminopyralid (150114-71-9) → methyl 4-amino-3-chloro-6-(4-chlorophenyl)picolinate (496850-17-0)

Conditions	Yield
Multi-step reaction with 4 steps 1: sulfuric acid / 24 h / Reflux; Inert atmosphere 2: 16 h / Reflux 3: potassium fluoride; bis-triphenylphosphine-palladium(II) chloride / water; acetonitrile / 0.33 h / 110 °C / Microwave irradiation; Sealed tube 4: acetyl chloride / methanol / 6 h View Scheme

aminopyralid (150114-71-9) → methyl 4-amino-3-chloro-6-(4-chloro-2-fluorophenyl)picolinate

Conditions	Yield
Multi-step reaction with 4 steps 1: sulfuric acid / 24 h / Reflux; Inert atmosphere 2: 16 h / Reflux 3: potassium fluoride; bis-triphenylphosphine-palladium(II) chloride / water; acetonitrile / 0.33 h / 110 °C / Microwave irradiation; Sealed tube 4: acetyl chloride / methanol / 6 h View Scheme

aminopyralid (150114-71-9) → 4-amino-3-chloro-6-(4-chloro-2-fluorophenyl)picolinic acid (496851-88-8)

Conditions	Yield
Multi-step reaction with 4 steps 1: sulfuric acid / 24 h / Reflux; Inert atmosphere 2: 16 h / Reflux 3: potassium fluoride; bis-triphenylphosphine-palladium(II) chloride / water; acetonitrile / 0.33 h / 110 °C / Microwave irradiation; Sealed tube 4: sodium hydroxide; water / methanol / 16 h / 20 °C View Scheme

aminopyralid (150114-71-9) → C11H10Cl2N2O4

Conditions	Yield
Multi-step reaction with 2 steps 1: sulfuric acid / 24 h / Reflux; Inert atmosphere 2: 16 h / Reflux View Scheme

aminopyralid (150114-71-9) → methyl 4-amino-5-bromo-3-chloro-6-(4-chloro-2-fluoro-3-methoxyphenyl)picolinate

Conditions	Yield
Multi-step reaction with 5 steps 1: sulfuric acid / 24 h / Reflux; Inert atmosphere 2: 16 h / Reflux 3: potassium fluoride; bis-triphenylphosphine-palladium(II) chloride / water; acetonitrile / 0.33 h / 110 °C / Microwave irradiation; Sealed tube 4: acetyl chloride / methanol / 6 h 5: N-Bromosuccinimide / dichloromethane / 3 h / 20 °C View Scheme

aminopyralid (150114-71-9) → 4-amino-3-chloro-6-(4-chloro-2-fluoro-3-methoxyphenyl)-2-pyridinecarboxylic acid

Conditions	Yield
Multi-step reaction with 4 steps 1: sulfuric acid / 24 h / Reflux; Inert atmosphere 2: 16 h / Reflux 3: potassium fluoride; bis-triphenylphosphine-palladium(II) chloride / water; acetonitrile / 0.33 h / 110 °C / Microwave irradiation; Sealed tube 4: sodium hydroxide; water / methanol / 16 h / 20 °C View Scheme
Multi-step reaction with 3 steps 1: thionyl chloride / 12 h / 65 °C / Cooling with ice 2: potassium fluoride; bis-triphenylphosphine-palladium(II) chloride / water; acetonitrile / 4 h / Reflux 3: sodium hydroxide; water / 8 h View Scheme

aminopyralid (150114-71-9) → methyl 4-(acetylamino)-3,6-dichloropyridine-2-carboxylate

Conditions	Yield
Multi-step reaction with 2 steps 1: sulfuric acid / 24 h / Reflux; Inert atmosphere 2: 16 h / Reflux View Scheme

aminopyralid (150114-71-9) → methyl 4-(acetylamino)-3-chloro-6-(4-chloro-2-fluoro-3-methoxyphenyl)pyridine-2-carboxylate (943831-44-5)

Conditions	Yield
Multi-step reaction with 3 steps 1: sulfuric acid / 24 h / Reflux; Inert atmosphere 2: 16 h / Reflux 3: potassium fluoride; bis-triphenylphosphine-palladium(II) chloride / water; acetonitrile / 0.33 h / 110 °C / Microwave irradiation; Sealed tube View Scheme

aminopyralid (150114-71-9) → C20H15Cl2FN4O3

Conditions	Yield
Multi-step reaction with 4 steps 1: thionyl chloride / 12 h / 65 °C / Cooling with ice 2: potassium fluoride; bis-triphenylphosphine-palladium(II) chloride / water; acetonitrile / 4 h / Reflux 3: sodium hydroxide; water / 8 h 4: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; dmap / dichloromethane View Scheme

Upstream product

• 2545-60-0 4-amino-3,5,6-trichloro-2-pyridinecarboxylic acid monopotassium salt 
• 1918-02-1 picloram 

Downstream Products

• 1918-02-1 picloram 
• 350601-39-7 methyl 4-amino-3,6-dichloropyridine-2-carboxylate 
• 943831-44-5 methyl 4-(acetylamino)-3-chloro-6-(4-chloro-2-fluoro-3-methoxyphenyl)pyridine-2-carboxylate 
• 496851-88-8 4-amino-3-chloro-6-(4-chloro-2-fluorophenyl)picolinic acid 
• 496850-17-0 methyl 4-amino-3-chloro-6-(4-chlorophenyl)picolinate 
• 496850-14-7 methyl 4-amino-3-chloro-6-phenylpicolinate 
• 943831-98-9 halauxifen methyl ester 
• 496850-54-5 methyl 4-acetamido-3-chloro-6-(4-chloro-2-fluorophenyl)picolinate 
• 496850-56-7 methyl 4-acetamido-3-chloro-6-(4-chlorophenyl)picolinate 

Relevant articles and documents

Method for preparing 4 - amino -3 and 6 - dichloro pyridine formic acid by electrochemical selective dechlorination

The invention discloses a method for preparing 4-amino-3,6-dichloropicolinic acid by electrochemical selective dechlorination. The method comprises the following steps: a diaphragm electrolytic tank is adopted, a 4-amino-3,5,6-trichloropyridine formate aqueous solution prepared from electronic-grade ultrapure water is used as a catholyte, an alkali metal hydroxide aqueous solution preparedfrom electronic-grade ultrapure water is used as an anolyte, a nickel-based material is used as an anode, and silver with purity of 99.95%-99.99% is used as a cathode; and an electrolysis reaction is carriedout under the conditions of a current density of 1-20 A/dm and a reaction temperature of 0-90 DEG C, after the electrolysis reaction is completed, the catholyte is separated and purified to obtainthe 4-amino-3,6-dichloropicolinic acid. According to the method provided by the invention, the catholyte and the anolyte are prepared by adopting the electronic-grade ultrapure water, the 4-amino-3,6-dichloropicolinic acid can be prepared through highly-selective dechlorination, the product yield is improved by 4-10%, and the purity is improved by 2-5%.

Method for preparing 4-amino-3,6-dichloropicolinic acid by reducing 4-amino-3,5,6-trichloropicolinic acid

The invention discloses a method for preparing 4-amino-3,6-dichloropicolinic acid by reducing 4-amino-3,5,6-trichloropicolinic acid, which belongs to the technical field of chemical products. Under the conditions of a specific temperature, specific pressure and a specific PH value, chlorine on a pyridine ring is removed by virtue of catalytic hydrogenation to prepare 4-amino-3,6-dichloropicolinic acid. In the method, a clean and environment-friendly catalytic hydrogenation process is used for high selectively hydrogenating and reducing the 4-amino-3,5,6-trichloropicolinic acid to prepare the 4-amino-3,6-dichloropicolinic acid, and poisonous hazardous articles such as the reducing agent hydrazine and dichloromethane are not used in the production process, so that the method is moderate in reaction condition, simple in devices, convenient to operate, capable of realizing zero emission from the production of 4-amino-3,6-dichloropicolinic acid, suitable for industrialized mass production and remarkable in economical advantage and environmental protection advantage.